Florida Keys Kiteboarding: Islamorada & Marathon

Closest airport: Miami International Airport and Key West International AirportBest wind: October to MayAverage wind: 15 to 25 knotsTop riders: Lots of Florida riders come here to train, as do many others. On any given day, you can find yourself riding with Alex Fox, Billy Parker, Rich Sabo, Eric Rienstra, Sean Reyngoudt, Tommy Fields and many more.

First time I came to the Florida Keys, I was barely old enough to remember it. It made a big enough impact on me at such a young age, though, that it paved a path for the direction my life would go. The Keys have been a destination for many influential people, long before you could just hop in your car and cruise from Miami to Key West. Ernest Hemingway, Jimmy Buffett, countless artists and even former U.S. presidents all had homes in the Keys, and favored them as their go-to getaway. Nowadays, especially for ocean enthusiasts, it’s simply the Caribbean you can drive to. Cold fronts bring several day spurts of wind throughout the winter months, providing unparalleled flatwater kiting. In-between fronts you can occupy your time with world-class sport fishing, lobstering, or honing your skills at the Keys Cable wake park that was opened last year by myself and oTHErside Boardsports.
In March and late spring, you can catch the Bermuda Highs that bring the cleanest winds to the Keys, which happens to be packed with spring break coeds and the warmest weather in the U.S. There’s a vibe you feel as soon as you get into the Keys, a vibe that can’t be justified by the words in this paragraph. Do yourself a favor and come experience it yourself. —Matt Sexton

The Florida Keys
Over a 120 miles of lush tropical islands that curve their way from Miami towards Havana, Cuba. Locals designate locations by their mile markers along the Overseas Highway, which stretches from Key Largo to Key West. Wind is predominately out of the east, which is good, as it provides the best direction for most park-and-ride locations, but local operations like oTHErside Boardsports and The Kitehouse will ferry you to clean wind in other directions. While the keys are very kiter-friendly, the locals ask only that you respect their beaches and steer clear of boats and fishermen, as they make their living off the fish that can be scared from the flats as kiters fly by.

The Scene
The scene is constantly changing depending on the time of year. While there is a solid presence of local riders, the majority of the scene is tourism based. Holidays will bring crowds to the beaches, since despite the fact you’re on an island, natural beaches are scarce. There are many launches throughout the Keys, but it’s recommended you check in with the local shop (OthersideBoardsports.com) before setting up and riding out somewhere.

The Slingshot crews kiteboarding roadtrip to the Florida Keys. Most of the riding is filmed in Islamorada and Marathon.Best LaunchesWhale Harbor: The northernmost launch available in the Keys. Whale is a kite concession operated by Brad Lange at Seven Sports, and is located at approximately mile marker (MM) 83.5. It is rideable from a northeast to a south-southwest, with awesome flatwater and plenty of room once on the water. On the beach, however, it’s tight quarters, so be sure to wrap your lines because they will get tangled. After your session, be sure to head up to Wahoos, the bar located on site, as they have a killer happy hour and a great view. The only downfall to this launch, aside from high quarters, is the $10 daily launching fee.

Anne’s Beach: Located at MM 72, Anne’s Beach is one of the top spots to ride in the Keys. Since the islands curve to the west the farther south they get, Anne’s requires a solid east wind for the cleanest conditions, and is rideable all the way around to a southwest. Kiters park in the southern parking lot, and space can be an issue, so arrive early. There’s a shower and a bathroom located in the northern lot, which is connected by a boardwalk through the mangroves. Again, the launch is small, so manage your space consumption well and watch your step, as the intertidal zone can be slick.

Hawks Cay and Keys Cable: Boat trips leave from here daily, with resort discounts for kiteboarders. If the wind dies, Keys Cable provides the best no-wind alternative in the Keys. Contact oTHErside Boardsports for more details.

Curry Hammock: MM 56Bahia Honda: MM 24Smathers Beach: Key West

All these beaches require east-southwest winds and have a variety of conditions. Curry and Bahia are both state parks with entrance fees, but have great amenities once inside. Bahia is also one of the largest natural beaches in the Keys and has some decent kickers if the wind’s been up for a few days. Smathers is the most crowded beach in the Keys, and kiteboarding is only allowed on the most eastern side closest to the airport.

Need to KnowGetting There
A quick drive from Miami or Fort Lauderdale airports, the Keys are extremely accessible. More airlines are now offering direct flights to Key West, too, but they are more costly and only worth it if you’re staying in the Southern Keys. When in the Keys, obey speed limits, especially in the Big Pine Area, as over six law enforcement agencies monitor the highways.

When To Go
The best months are December through March, with both December and March being the most consistent. While it is the southernmost point in the U.S., don’t be fooled into forgetting your wetsuits. Cold fronts are largely what bring the wind during these months, and in January and February, the cold but still humid air will feel brisk.

Where To Stay
Depending on whether you’d like to be in the Northern or Southern Keys, there are a bunch of options ranging in price. There are state parks to camp in, and price-point motels for those traveling on a budget. Or if you’re looking for a real Keys experience, head to Hawks Cay or one of the smaller bed and breakfasts located in Old Town in Keys West.

Where To EatDinner: Amigo’s Taqueria right off Duval Street is kiter-owned, and the food is great.Lunch: Lunch is really just an extension of breakfast in the Keys, so hit up any of the recommended breakfast places and go for some fish tacos or a Cuban mix sandwich.Breakfast: In Islamorada, hit up Village Gourmet for a breakfast burrito. In the Southern Keys, hit up 5 Brothers Grocery, or Sandy’s for a strong Cuban coffee and a great egg sandwich on flatbread.

Keys Cable ParkWhen it’s not windy, go to the Keys Cable Park to work on your board skills or grab a set with some pros. After that, head up to Robbie’s to feed the Tarpon, or head south to Key West and experience the Duval Crawl and daytime debauchery Key Weird has to offer….

Matthew Sexton has been kiteboarding for 10 years and has taught over 500 lessons. Matt continues to develop state-of-the-art ways to teach people to kiteboard, and still rides professionally for the Slingshot global team, as well as several other brands.